Synthesis of quinoxaline analogues

Synthesis

Volumn , Issue 19, 2011, Pages 3143-3151

  Chang, Meng Yang ^a   Lee, Tein Wei ^a   Hsu, Ru Ting ^b   Yen, Tzu Lin ^c  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b ShuZen College of Medicine and Management   (Taiwan)

^c KAOHSIUNG MUNICIPAL HSIAO KANG HOSPITAL   (Taiwan)

Author keywords

arenes; condensation; halogenation; heterocycles; tandem reactions

Indexed keywords

ARENES; CYCLIC KETONES; HETEROCYCLES; HIGH YIELD; N-BROMOSUCCINIMIDE; QUINOXALINES; TANDEM REACTION;

CONDENSATION; HALOGENATION; KETONES;

ORGANIC COMPOUNDS;

1,2,3,4 TETRAHYDROPHENAZINE; 11H INDENO[1,2 B]QUINOXALINE; 2 (METHYLPHENYL)SULFONYL 1,2,3,4 TETRAHYDROPYRIDO[3,4 B]QUINOXALINE; 2 BENZENESULFONYL 1,2,3,4 TETRAHYDROPYRIDO[3,4 B]QUINOXALINE; 2 ETHYL 1,2,3,4 TETRAHYDROPHENAZINE; 2 ETHYL 7 (2 ETHYL 1,2,3,4 TETRAHYDROPHENAZIN 7 YL) 1,2,3,4 TETRAHYDROPHENAZINE; 2 METHANESULFONYL 1,2,3,4 TETRAHYDROPYRIDO[3,4 B]QUINOXALINE; 2 METHYL 1,2,3,4 TETRAHYDROPHENAZINE; 2,3 DIHYDRO 1H CYCLOPENTA[B]QUINOXALINE; 2,3 DIHYDRO 6 (2,3 DIHYDRO 1H CYCLOPENTA[B]QUINOXALIN 7 YL) 1H CYCLOPENTA[B]QUINOXALINE; 3,4 DIHYDRO 1H PYRANO[3,4 B]QUINOXALINE; 5 METHYL BENZO[A]PHENAZINE; 6,7 DIHYDRO 5H 8,13 DIAZABENZO[3,4]CYCLOHEPTA[1,2 B]NAPHTHALENE; 6,7,8,9 TETRAHYDROPYRIDO[3,4 B]QUINOXALINE; 6,7,8,9,10,11 HEXAHYDRO CYCLOOCTA[B]QUINOXALINE; 6,7,8,9,10,11,12,13,14,15 DECAHYDRO 2,5,16 TRIAZACYCLODODECA[B]NAPHTHALENE; 6,7,8,9,10,11,12,13,14,15 DECAHYDRO 5,16 DIAZACYCLODODECA[B]NAPHTHALENE; 7 METHYL 6,7,8,9 TETRAHYDROPYRIDO[3,4 B]QUINOXALINE; 7,8,9,10 TETRAHYDRO 2 (7,8,9,10 TETRAHYDRO 6H CYCLOHEPTA[B]QUINOXALIN 3 YL) 6H CYCLOHEPTA[B]QUINOXALINE; 7,8,9,10 TETRAHYDRO 6H CYCLOHEPTA[B]QUINOXALINE; 8 METHYL 6,7,8,9 TETRAHYDROPYRIDO[3,4 B]QUINOXALINE; BENZO[A]PHENAZINE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; BROMINATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; HALOGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 80053051607     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260147     Document Type: Article

References (45)

1. Comprehensive Heterocyclic Chemistry II Vol. 6 Sato N Katritzky A R. Rees C W. Scriven E F. V. Pergamon Press Oxford 1996 233
2. Seitz L E., Suling W J., Reynolds R C., J. Med. Chem. 2002 45 5604
3. Kamal A, Reddy K L., Devaiah V, Shankaraiah N, Rao M V., Mini-Rev. Med. Chem. 2006 6 71
4. Chen Q, Bryant V C., Lopez H, Kelly D L., Luo X, Natarajan A, Bioorg. Med. Chem. Lett. 2011 21 1903
5. You L, Cho E J., Leavitt J, Ma L.-C, Montelione G T., Anslyn E V., Krug R M., Ellington A, Robertus J D., Bioorg. Med. Chem. Lett. 2011 21 3007
6. Porter A E. A., Comprehensive Heterocyclic Chemistry Pergamon Oxford 1984
7. Brown D J., The Chemistry of Heterocyclic Compounds John Wiley & Sons New Jersey 2004
8. For Bi(0), see:, Antoniotti S, Dunach E, Tetrahedron Lett. 2002 43 3971
9. For PEG400, see:, Cho C S., Ren W X., Shim S C., Tetrahedron Lett. 2007 48 4665
10. Padmavathy K, Nagendrappa G, Geetha K V., Tetrahedron Lett. 2011 52 544
11. For green chemistry, see:, Huang T, Zhang Q, Chen J, Gao W, Ding J, Wu H, J. Chem. Res. 2009 12 761
12. More S V., Sastry M N. V., Yao C.-F, Green Chem. 2006 8 91
13. Sarkis G Y., Al-Azawe S, J. Chem. Eng. Data 1973 18 102
14. For solid-phase chemistry, see:, Wu Z, Ede N J., Tetrahedron Lett. 2001 42 8115
15. Singh S K., Gupta P, Duggineni S, Kundu B, Synlett 2003 2147
16. Das B, Venkateswarlu K, Suneel K, Majhi A, Tetrahedron Lett. 2007 48 5371
17. For solid-phase extraction, see:, Kowalski J A., Leonard S F., Lee G E. Jr., J. Comb. Chem. 2006 8 774
18. For microwave irradiation, see:, Zhao Z, Wisnoski D D., Wolkenberg S E., Leister W H., Wang Y, Lindsley C W., Tetrahedron Lett. 2004 45 4873
19. Xekoukoulotakis N P., Hadjiantoniou-Maroulis C P., Maroulis A J., Tetrahedron Lett. 2000 41 10299
20. Kim S Y., Park K H., Chung Y K., Chem. Commun. 2005 1321
21. Kim S Y., Park K H., Chung Y K., Chem. Commun. 2005 1321
22. Jeena V, Robinson R S., Beilstein J. Org. Chem. 2009 5 24
23. Shaabani A, Maleki A, Chem. Pharm. Bull. 2008 56 79
24. Slusarczyk M, deBorggraeve W M., Toppet S, Hoornaert G J., Eur. J. Org. Chem. 2007 2987
25. For iodine, see:, Bhosale R S., Sarda S R., Ardhapure S S., Jadhav W N., Bhusare S R., Pawar R P., Tetrahedron Lett. 2005 46 7183
26. More S V., Sastry M N. V., Wang C.-C, Yao C.-F, Tetrahedron Lett. 2005 46 6345
27. For sulfamic acid, see:, Darabi H R., Mohandessi S, Aghapoor K, Mohsenzadeh F, Catal. Commun. 2007 8 389
28. For Ni nanoparticles, see:, Kumar A, Kumar S, Saxena A, De A, Mozumdar S, Catal. Commun. 2008 9 778.
29. 2:, Robinson R S., Taylor R J. K., Synlett 2005 1003
30. 3]:, Cho C S., Oh S G., Tetrahedron Lett. 2006 47 5633
31. 2:, Kotharkar S A., Shinde D B., Bull. Korean Chem. Soc. 2006 27 1466
32. 2:, Cho C S., Oh S G., J. Mol. Catal. A: Chem. 2007 205
33. 3]:, Cai J J., Zou J P., Pan X Q., Zhang W, Tetrahedron Lett. 2008 49 7386
34. 2:, Raw S A., Wilfred C D., Taylor R J. K., Chem. Commun. 2003 2286
35. Venkatesh C, Singh B, Mahata P K., Ila H, Junjappa H, Org. Lett. 2005 7 2169
36. daSilva M J., Pinto M C. F. R., deSimone C A., Soares J G., Reys J R. M., Filho J D. S., Harrison W T. A., Carvalho C E. M., Goulart M O. F., Jnior E N. S., Pinto A V., Tetrahedron Lett. 2011 52 2415
37. Veisi H, Ghorbani-Vaghei R, Tetrahedron 2010 66 7445
38. Qi C, Jiang H, Huang L, Chen Z, Chen H, Synthesis 2011 387
39. Kuo C.-W, More S V., Yao C.-F, Tetrahedron Lett. 2006 47 8523
40. Chang M.-Y, Lee T.-W, Lin C.-H, Tetrahedron 2011 67 4892
41. Emoto T, Kubosaki N, Yamagiwa Y, Kamikawa T A., Tetrahedron Lett. 2000 41 355
42. deAndrade-Neto V F., Goulart M O. F., daSilvaFilho J F., daSilva M J., Pinto M C. F. R., Pinto A V., Zalis M G., Carvalho L H., Krettli A U., Bioorg. Med. Chem. Lett. 2004 14 1145
43. Makgatho M E., Anderson R, OSullivan J F., Egan T J., Freese J A., Cornelius N, vanRensburg C E. J., Drug Dev. Res. 2000 50 195
44. Wang W Y., Preville P, Morin N, Mounir S, Cai W Z., Siddiqui M A., Bioorg. Med. Chem. Lett. 2000 10 1151
45. CCDC 807121 (3b), 810169 (3h), 818140 (3m), and 818141 (3o) contain the supplementary crystallographic data for this paper. This data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk].